Azetidine → (2S)-1-{[6-(1-Azetidinyl)-4-methyl-3-pyridinyl]carbonyl}-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine

HRID 43428Notes

Reaction equation

F[C:2]1[N:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:15][CH2:14][N:13]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH2:12][C@@H:11]2[CH3:29])=[O:9])=[C:4]([CH3:30])[CH:3]=1.[NH:31]1[CH2:34][CH2:33][CH2:32]1>C(O)(C)C>[N:31]1([C:2]2[N:7]=[CH:6][C:5]([C:8]([N:10]3[CH2:15][CH2:14][N:13]([S:16]([C:19]4[CH:20]=[CH:21][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:23][CH:24]=4)(=[O:18])=[O:17])[CH2:12][C@@H:11]3[CH3:29])=[O:9])=[C:4]([CH3:30])[CH:3]=2)[CH2:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 120 °C

Procedure

(2S)-1-[(6-Fluoro-4-methyl-3-pyridinyl)carbonyl]-2-methyl-4-{[4-(trifluoromethyl)phenyl]sulfonyl}piperazine (may be prepared as described in Example 27) (67 mg, 0.15 mmol) was weighed into a microwave vial and dissolved in isopropanol (1.5 ml). Azetidine (0.203 ml, 3.01 mmol) was added and the mixture was heated in the microwave to 120° C. for 12 h with stirring. The reaction mixture was concentrated to give the crude material as a colourless gum (˜187 mg). This was purified by MDAP to give the title compound as a pale yellow gum (67 mg). The gum was redissolved in MeOH, water was added, and the mixture was concentrated under a flow of argon then dried in vacuo to give the title compound as a colourless solid.

Workup

concentrationThe reaction mixture was concentrated
customto give the crude material as a colourless gum (˜187 mg)
customThis was purified by MDAP

Sources & evidence

ORD record: ord-dbeaac187aa34fe3a5007b1b71b9da9b
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536183B2

Reaction notes

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